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Acetic Acid → HCID 178491006, compound

HRID 2040645
Notes
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Reaction equation

HRID 2040645 reaction equation
[NH2:1][CH2:2][C@@H:3]1[C@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@H:6]2[C@H:5]([N:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=4[O:32][CH3:33])[C:16]=3[CH:15]=[CH:14]2)[CH2:4]1.[Cl:34][C:35]1[C:36]([C:51]([F:54])([F:53])[F:52])=[CH:37][C:38]2[N:42]=[C:41]([CH2:43][CH2:44][CH:45]3[CH2:48][C:47](=O)[CH2:46]3)[NH:40][C:39]=2[CH:50]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[Cl:34][C:35]1[C:36]([C:51]([F:54])([F:52])[F:53])=[CH:37][C:38]2[N:42]=[C:41]([CH2:43][CH2:44][CH:45]3[CH2:46][CH:47]([NH:1][CH2:2][C@@H:3]4[C@H:7]5[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@H:6]5[C@H:5]([N:13]5[C:17]6[N:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][C:24]7[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=7[O:32][CH3:33])[C:16]=6[CH:15]=[CH:14]5)[CH2:4]4)[CH2:48]3)[NH:40][C:39]=2[CH:50]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 677749937-((3aS,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-N-(2,4-dimethoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 178515984HCID 178515984, compound

Product 1

HCID 178491006HCID 178491006, compound
Yield 72%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7-((3aS,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-N-(2,4-dimethoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (80 mg, 0.18 mmol) and 3-(2-(6-chloro-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)ethyl)cyclobutanone (45 mg, 0.14 mmol) in 1,2-dichloroethane (2.4 mL) was treated dropwise with acetic acid (10 uL, 0.18 mmol). The solution was treated with sodium triacetoxyborohydride (53 mg, 0.25 mmol) in one portion and allowed to stir at room temperature till complete by HPLC. After 4 h, the reaction mixture was diluted with 10 mL CH2Cl2 and washed with 10 mL sat NaHCO3. The aqueous phase was washed with 10 mL CH2Cl2 and the combined organic phase was dried over Na2SO4. The solution was filtered and concentrated to yield a light tan glass/stiff foam. The crude material was purified by flash chromatography (25 g silica gel; 5% 7N NH3 in CH3OH/CHCl3) to yield the title compound (76 mg, 71%) as a colorless glass/stiff foam: MS (ESI+) for C38H43ClF3N7O4 m/z 754.3 (M+H)+; MS (ESI−) for C38H43ClF3N7O4 m/z 752.3 (M−H)−; HPLC purity 90.5% (ret. time, 3.24 min).

Workup

  1. washwashed with 10 mL
  2. washThe aqueous phase was washed with 10 mL CH2Cl2
  3. dry with materialthe combined organic phase was dried over Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customto yield a light tan glass/stiff foam
  7. customThe crude material was purified by flash chromatography (25 g silica gel; 5% 7N NH3 in CH3OH/CHCl3)

Sources & evidence

ORD record
ord-8aa5c0872ff247a4ab6229bfc5bec5ab
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580762B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes